EP1455602B1 - Modified methionine rich food products and process for their manufacture - Google Patents

Modified methionine rich food products and process for their manufacture Download PDF

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Publication number
EP1455602B1
EP1455602B1 EP02792103A EP02792103A EP1455602B1 EP 1455602 B1 EP1455602 B1 EP 1455602B1 EP 02792103 A EP02792103 A EP 02792103A EP 02792103 A EP02792103 A EP 02792103A EP 1455602 B1 EP1455602 B1 EP 1455602B1
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EP
European Patent Office
Prior art keywords
food product
meth
cysteine
methionine
serine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP02792103A
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German (de)
English (en)
French (fr)
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EP1455602A1 (en
Inventor
Petra Verhoef
Roelof Van Der Meer
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DSM IP Assets BV
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DSM IP Assets BV
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Publication date
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Priority to EP02792103A priority Critical patent/EP1455602B1/en
Publication of EP1455602A1 publication Critical patent/EP1455602A1/en
Application granted granted Critical
Publication of EP1455602B1 publication Critical patent/EP1455602B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C19/00Cheese; Cheese preparations; Making thereof
    • A23C19/06Treating cheese curd after whey separation; Products obtained thereby
    • A23C19/09Other cheese preparations; Mixtures of cheese with other foodstuffs
    • A23C19/0921Addition, to cheese or curd, of minerals, including organic salts thereof, trace elements, amino acids, peptides, protein hydrolysates, nucleic acids, yeast extracts or autolysate, vitamins or derivatives of these compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00Milk preparations; Milk powder or milk powder preparations
    • A23C9/12Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/1322Inorganic compounds; Minerals, including organic salts thereof, oligo-elements; Amino-acids, peptides, protein-hydrolysates or derivatives; Nucleic acids or derivatives; Yeast extract or autolysate; Vitamins; Antibiotics; Bacteriocins
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L13/00Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/428Addition of flavours, spices, colours, amino acids or their salts, peptides, vitamins, yeast extract or autolysate, nucleic acid or derivatives, organic acidifying agents or their salts or acidogens, sweeteners, e.g. sugars or sugar alcohols; Addition of alcohol-containing products
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L15/00Egg products; Preparation or treatment thereof
    • A23L15/30Addition of substances other than those covered by A23L15/20 – A23L15/25
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15Vitamins
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17Amino acids, peptides or proteins
    • A23L33/175Amino acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention is concerned with methionine rich food products, e.g. food products comprising significant amounts of animal derived protein or proteinaceous material derived from seeds, nuts, grain or pulses, which products have been modified so as to reduce their boosting effect on serum homocysteine concentration. More particularly, the invention is concerned with food products comprising at least 5% proteinaceous matter by weight of dry matter, wherein at least 50% of the proteinaceous matter is of animal origin or derived from seeds, nuts, grain or pulses, and wherein the amino acid profile of the food product has been altered to contain elevated amounts of cysteine, and optionally serine.
  • Another aspect of the invention is concerned with a method of modifying a methionine rich food product by incorporating therein a source of cysteine, and optionally a source of serine.
  • Homocysteine (HS-CH 2 -CH(NH 2 )-COOH) is a substance which has attracted significant scientific interest because of its association with the development of cardiovascular diseases. Numerous scientific studies have shown that patients suffering from myocardial infarction, stroke, or peripheral occlusive arterial disease, exhibit elevated serum homocysteine concentration (hyperhomocysteinemia). A high concentration of homocysteine is regarded a risk factor for cardiovascular disease. Hyperhomocysteinemia has also been associated with other health risks, e.g. manic depressions, seizure disorders, depression, asthma and migraine headaches.
  • methionine rich food products may confer a methionine load which will subsequently cause a substantial increase in plasma homocysteine concentration. Consequently, individuals who are at risk of cardiovascular diseases, would be well advised not to consume methionine rich food products, e.g. dairy and meat products.
  • the main metabolic pathways for reducing plasma homocysteine levels are:
  • WO 97/34497 describes dairy products having a modified methionine : vitamin B6 ratio (mg/mg) comprising (a) dairy products having a base methionine : vitamin B6 ratio and (b) at least one source of vitamin B6 present in an amount sufficient to modify the base methionine : vitamin B6 ratio to a reduced preselected ratio.
  • a modified methionine : vitamin B6 ratio (mg/mg) comprising (a) dairy products having a base methionine : vitamin B6 ratio and (b) at least one source of vitamin B6 present in an amount sufficient to modify the base methionine : vitamin B6 ratio to a reduced preselected ratio.
  • the amount of the cofactors of the methionine metabolism in particular of vitamin B6, and optionally of magnesium, folic acid, vitamin B12, and cysteine are increased.
  • US 5,795,873 (Allen) describes a method of treating or preventing elevated serum metabolite levels of homocysteine, comprising periodically administering orally a single formulation having between 0.3-10 mg vitamin B12 and 0.1-0.4 mg folic acid.
  • the option of co-administering vitamin B6 is also mentioned.
  • vitamin B6, B12, betaine and folic acid may suitably be used in the treatment of hyperhomocysteinemia, such treatments are often insufficient to restore serum homocysteine levels to normal levels.
  • individuals suffering from hyperhomocysteinemia are well advised to follow a strict diet in which they are not allowed to consume high methionine food products. Since dairy products and meat products are generally regarded as methionine rich food products, such a diet prevents the individual from consuming palatable and nutritionally important foodstuffs.
  • hyperhomocysteinemia may be treated and/or prevented without the need for a diet that precludes the consumption of methionine rich food products. It was discovered that the amino acid profile of methionine rich food products may be altered in such a way that the high levels of methionine contained in such products will not automatically lead to significantly enhanced serum homocysteine levels. In particular, it was unexpectedly established that cysteine has an antagonistic effect on the serum homocysteine elevating effect of methionine, particularly when used in combination with serine.
  • cysteine and serine are involved in the metabolisation of homocysteine. It would appear that the ratio in which cysteine and methionine are present in an ingested food product determines the extent to which the ingested methionine will give rise to elevated serum homocysteine concentrations. Thus, even in case of food products containing high levels of methionine, the undesired effects on serum homocysteine levels may be suppressed by adjusting the amino acid balance and particularly the ratio of methionine versus cysteine and optionally the ratio of methionine versus serine.
  • the benefits of the present invention are particularly appreciated in food products which contain significant amounts of proteinaceous material of animal origin, notably milk, meat, eggs, fish and shellfish, or proteinaceous material derived from seeds, nuts, grain or pulses.
  • proteinaceous material of animal origin notably milk, meat, eggs, fish and shellfish, or proteinaceous material derived from seeds, nuts, grain or pulses.
  • the proteinaceous material found in these foodstuffs and food components usually contains relatively high levels of methionine calculated on total amino acids.
  • one aspect of the invention is concerned with a methionine rich food product, i.e. a food product comprising at least 5 % proteinaceous matter by weight of dry matter, wherein at least 50 wt.% of the proteinaceous matter is of animal origin and/or derived from seeds, nuts, grain or pulses, said food product containing the amino acids cysteine [Cys], methionine [Meth] in a molar ratio which meets the following equation: [Cys] / [Meth] ⁇ 2:1.
  • amino acid e.g. methionine or [Meth]
  • said reference is meant to include corresponding amino acid residues.
  • sources of amino acid residues are proteins, oligopeptides, dipeptides, glycoproteins, lipoproteins etc.
  • cystine is considered to comprise 2 cysteine residues.
  • proteinaceous matter encompasses amino acids, (oligo)peptides and proteins, as well as any other substances that comprise amino acids, peptides (e.g. glycopeptides) and/or proteins (e.g. lipoproteins).
  • proteinaceous matter of animal origin examples include milk protein, meat protein, egg protein, and collagen, as well fractions thereof, e.g. casein, whey protein, meat hydrolysate etc.
  • animal as used in here not only encompasses vertebrates, but also birds, fish and shellfish. Also in meat obtained from fish and birds high levels of methionine are found.
  • the detrimental effect of a methionine rich food product on serum homocysteine levels may be suppressed in a particularly effective manner, if cysteine and methionine are present in a molar ratio of at least 3:1.
  • a significant amount of serine is incorporated in the present foodstuff so as to alter the amino acid profile in such a way that a molar ratio is obtained which meets the following equation: [Ser] /[Meth] ⁇ 4:1. Even more preferably, the molar ratio [Ser] / [Meth] is at least 6:1, most preferably at least 8:1.
  • the benefits of the present invention are most pronounced in food products containing methionine in relatively high amounts, calculated on the total amount of amino acids present therein. Consequently, in a preferred embodiment, the present food product contains methionine in a concentration which exceeds 1 mol.%, even more preferably exceeds 2 mol.%, calculated on the total amount of amino acids contained in the product.
  • the food product comprises at least 10%, more preferably at least 20% proteinaceous material by weight of dry matter.
  • the proteinaceous material is of animal origin.
  • the proteinaceous material of animal origin is suitably selected from the group consisting of milk, meat, egg, fish, shellfish, collagen, skin as well as food materials derived therefrom.
  • the animal source of the proteinaceous material is cattle, pig, sheep, goat, poultry or fish.
  • the ratio's in which methionine, cysteine and serine are represented in the food product according to the present invention may vary considerably, provided the combined level of cysteine and serine is sufficiently high to compensate for the homocysteine elevating effect of methionine which is present in the same product.
  • the present food product contains cysteine in an amount relative to its methionine content in accordance with the following equation: [Cys]/[Meth] ⁇ 4:1.
  • the minimum amount of serine present in the food product according to the invention is most preferably described by the following equationL [Ser]/[Meth] ⁇ 10:1.
  • the present food product preferably contains cysteine and serine in a ratio which is described by the following equation: 0.05 ⁇ [Cys]/[Ser] ⁇ 2.
  • the food product contains cysteine and serine in the following ratio: 0.1 ⁇ [Cys]/[Ser] ⁇ 1.
  • the benefits of the present invention may become manifest in any food products that contain proteinaceous matter with relatively high levels of methionine. It will be understood, however, that in particular food products containing significant amounts of protein may benefit from the present invention.
  • the present food product comprises at least 10 wt.%, preferably at least 20 wt.% proteinaceous matter.
  • the food product contains at least 10 mg/kg vitamin B6 or a precursor thereof.
  • precursor encompasses any substances which, following ingestion of the food product, are capable of liberating the active component (vitamin B6 or a physiologically active metabolite thereof) in the gastointestinal tract or after absorption into the body, e.g. as a result of metabolic breakdown in the liver.
  • Betaine is another co-factor of homocysteine metabolism, which may advantageously be included in the present food product.
  • the food product contains betaine and methionine [Meth] in a molar ratio which meets the following equation: [Bet]/[Meth] ⁇ 1: 1.
  • the present food products may suitably be used as (part of) a treatment or prophylactic treatment of hyperhomocysteinemia
  • another aspect of the invention is concerned with a method of (prophylactically) treating individuals suffering from elevated serum homocysteine levels. Consequently, the invention also relates to food products, as described herein before, for use in a method of treating or preventing elevated plasma concentrations of homocysteine.
  • Yet another aspect of the present invention relates to a method of modifying a methionine rich food product which contains methionine and optionally cysteine in a molar ratio which meets the following equation: [Cys]/[Meth] ⁇ 1:1, wherein the method comprises the incorporation of a source of cysteine in an amount sufficient to increase said ratio to more than 2:1, preferably to more than 4:1.
  • the food product optionally contains serine in a molar ratio which meets the following equation: [Ser]/[Meth] ⁇ 3:1, wherein the method comprises the incorporation of a source of serine in an amount sufficient to increase said ratio to more than 4:1, preferably to more than 6:1.
  • source of cysteine and/or serine should be understood to include materials which contain cysteine and/or serine in the form of free amino acids and/or amino acid residues.
  • the source of cysteine and the source of serine may be any foodgrade material that contains relatively high levels of cysteine and/or serine in comparison to methionine.
  • the source of cysteine contains cysteine and optionally methionine in the following molar ratio: [Cys]/[Meth] ⁇ 5:1. More preferably said ratio is at least 8:1.
  • the source of serine preferably contains serine and optionally methionine in the following molar ratio: [Ser]/[Meth] ⁇ 8:1. More preferably the latter ratio is at least 12:1.
  • the source of cysteine as well as the source of serine is a protein concentrate comprising at least 40%, preferably at least 60% proteinaceous matter by weight of dry matter.
  • the source of cysteine preferably contains cysteine in an amount of at least 5%, preferably at least 8% by weight of the proteinaceous matter.
  • the source of serine preferably contains serine in an amount of at least 8%, preferably at least 12% by weight of the proteinaceous matter.
  • the source of cysteine and the source of serine are incorporated in an amount which does not exceed 25 wt.% of the original food product. More preferably said amount does not exceed 10 wt.%.
  • the proteinaceous matter contained by the source of cysteine and the source of serine has a degree of hydrolysis of at least 50%, more preferably a degree of hydrolysis of at least 80%.
  • the sources of cysteine and serine may suitably have been hydrolysed to a sufficient degree by means of enzymatic hydrolysis.
  • reaction flavours or processed flavours
  • Such reaction flavours are particularly useful for imparting meaty and nutty flavour notes to foodstuffs.
  • the present invention does not comprise the inclusion of such a reaction flavour, since the reactions occurring during the heating process converts cysteine into components that do not have an antagonistic effect on the serum homocysteine elevating effect of methionine
  • the present method may advantageously be employed in the manufacture of dairy and meat derived foodstuffs.
  • the source of cysteine and/or serine used in the present method preferably is of the same animal origin as the bulk of the food product.
  • the food product comprises at least 5 % proteinaceous matter by weight of dry matter, at least 50 wt.% of the proteinaceous matter being of animal origin, and wherein the source of cysteine and/or serine is of the same animal origin as said proteinaceous matter.
  • suitable sources of cysteine and/or serine include whey (particularly lactalbumin), protein or protein fractions isolated from pulses and wheat proteins (especially albumine and globuline).
  • whey particularly lactalbumin
  • protein or protein fractions isolated from pulses and wheat proteins especially albumine and globuline.
  • an amino acid and/or peptide isolation technique Such isolation techniques are well known in the art and include, for instance, ion exchange, gel permation and reversed phase chromatogaphy, as well as ultrafiltration, nanoflitration and precipitation.
  • Yet another aspect of the present invention relates to the use of the combination of cysteine and serine in a product selected from the group of foodstuffs, nutritional products and pharmaceutical preparations, for lowering the serum homocysteine elevating effect of the product and/or for increasing the serum homocysteine lowering effect of the product.
  • the present invention also encompasses a method of treating or preventing hyperhomocysteinemia in humans by orally administering an effective amount of a food product as defined herein before.
  • compositions described in the above table control, composition I, composition II, composition III
  • the 4 different compositions are ingested by each subject in random order on days 2, 9, 16 and 23.
  • Blood serum homocysteine levels are measured 0, 2, 4, 6, 8, 10 and 24 hours after breakfast. Homocysteine is found to increase considerably after the subjects have ingested the control composition. The observed increase in homocysteine level is significantly lower after subjects have ingested composition I or II than after the control composition. The increase in homocysteine level is found to be minimal after subjects have ingested composition III.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Mycology (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Microbiology (AREA)
  • Pulmonology (AREA)
  • Psychiatry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Dairy Products (AREA)
  • Seeds, Soups, And Other Foods (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Confectionery (AREA)
EP02792103A 2001-12-21 2002-12-20 Modified methionine rich food products and process for their manufacture Expired - Lifetime EP1455602B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP02792103A EP1455602B1 (en) 2001-12-21 2002-12-20 Modified methionine rich food products and process for their manufacture

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP01205069 2001-12-21
EP01205069 2001-12-21
PCT/NL2002/000854 WO2003055335A1 (en) 2001-12-21 2002-12-20 Modified methionine rich food products and process for their manufacture
EP02792103A EP1455602B1 (en) 2001-12-21 2002-12-20 Modified methionine rich food products and process for their manufacture

Publications (2)

Publication Number Publication Date
EP1455602A1 EP1455602A1 (en) 2004-09-15
EP1455602B1 true EP1455602B1 (en) 2006-03-08

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EP02792103A Expired - Lifetime EP1455602B1 (en) 2001-12-21 2002-12-20 Modified methionine rich food products and process for their manufacture

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US (1) US20040265358A1 (ja)
EP (1) EP1455602B1 (ja)
JP (1) JP4317023B2 (ja)
KR (1) KR20040077682A (ja)
CN (1) CN1317979C (ja)
AT (1) ATE319330T1 (ja)
AU (1) AU2002358347B2 (ja)
BR (1) BR0215274A (ja)
DE (1) DE60209793T2 (ja)
ES (1) ES2260500T3 (ja)
PL (1) PL205028B1 (ja)
RO (1) RO122116B1 (ja)
RU (1) RU2305417C2 (ja)
WO (1) WO2003055335A1 (ja)

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FI122914B (fi) * 2005-04-01 2012-08-31 Biohit Oyj Elintarvikekoostumus asetaldehydin sitomiseksi suussa ja ruoansulatuskanavassa ja menetelmä koostumuksen valmistamiseksi
US20110086803A1 (en) 2006-11-02 2011-04-14 Andre Leonardus De Roos Peptides containing tryptophan
CN103189499B (zh) * 2010-08-19 2016-08-10 株式会社明治 乳酸菌和/或双歧杆菌的存活能力提高剂
JP7305361B2 (ja) * 2019-01-31 2023-07-10 株式会社ヤクルト本社 還元型グルタチオン含有乳酸菌培養物の製造法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56110617A (en) * 1980-02-08 1981-09-01 Ajinomoto Co Inc Nutrient composition for young child
JPS60145067A (ja) * 1984-01-09 1985-07-31 Takeda Chem Ind Ltd 肉類食品の退色防止方法および退色防止用組成物
AU8033487A (en) * 1986-09-10 1988-04-07 Dudrick Medical Research Fund I. Ltd. Method and substrate composition for treating atherosclerosis
JP2990686B2 (ja) * 1994-11-17 1999-12-13 田辺製薬株式会社 水溶性ビタミンb類配合総合輸液
IL117505A (en) * 1996-03-15 1999-09-22 Niva Shapira Enriched dairy products
US5993866A (en) * 1997-09-12 1999-11-30 Shapira; Niva Process of making food products having reduced methionine ratios
JP2003503038A (ja) * 1999-06-29 2003-01-28 ザ・ニュージーランド・ミルク・インスティチュート・リミテッド 乳を主成分とする予防的補助食品

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US20040265358A1 (en) 2004-12-30
WO2003055335A1 (en) 2003-07-10
ES2260500T3 (es) 2006-11-01
CN1317979C (zh) 2007-05-30
EP1455602A1 (en) 2004-09-15
RU2305417C2 (ru) 2007-09-10
JP2005512584A (ja) 2005-05-12
KR20040077682A (ko) 2004-09-06
CN1612698A (zh) 2005-05-04
AU2002358347B2 (en) 2007-09-06
JP4317023B2 (ja) 2009-08-19
RO122116B1 (ro) 2009-01-30
DE60209793T2 (de) 2006-11-30
ATE319330T1 (de) 2006-03-15
RU2004122399A (ru) 2005-03-27
BR0215274A (pt) 2005-05-10
PL370830A1 (en) 2005-05-30
AU2002358347A1 (en) 2003-07-15
PL205028B1 (pl) 2010-03-31
DE60209793D1 (de) 2006-05-04

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